1-Ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene → Ethyl4-[4-(1-benzyloxycyclopropyl)-3-ethyl-phenylethynyl]-benzoate

HRID 51740

반응식

HRID 51740 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][CH2:10]2)=[C:5]([CH2:20][CH3:21])[CH:4]=1)#[CH:2].C(O)(=O)C1C=CC=CC=1.[CH2:31]([O:33][C:34](=[O:42])[C:35]1[CH:40]=[CH:39][C:38](I)=[CH:37][CH:36]=1)[CH3:32]>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:13]([O:12][C:9]1([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[C:2][C:38]3[CH:39]=[CH:40][C:35]([C:34]([O:33][CH2:31][CH3:32])=[O:42])=[CH:36][CH:37]=3)=[CH:4][C:5]=2[CH2:20][CH3:21])[CH2:11][CH2:10]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

참가 물질

6

반응물 2

HCID 225689831-Ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene2회HCID 69887287Ethyl-4-iodo-benzoate benzoate2회

생성물 1

HCID 22568992Ethyl4-[4-(1-benzyloxycyclopropyl)-3-ethyl-phenylethynyl]-benzoate수율 72%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

실험 절차

Using General Procedure F; 1-ethynyl-4-(1-benzyloxycyclopropyl)-3-ethyl-benzene (Intermediate 90, 90.0 mg, 0.33 mmol) and ethyl-4-iodo benzoate (Reagent A, 100.0 mg, 0.36 mmol) in triethylamine (5 mL) was treated with copper(I)iodide (21.0 mg, 0.11 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (77 mg, 0.11 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-4% EtOAc-hexanes) afforded 100.0 mg (72%) of the title compound.

후처리

  1. customsparged with argon for 5 minutes

출처 및 근거

ORD 기록
ord-1b781f55accc43c9b1b27ad6a6104566
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713647B2

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